The reagents used for the synthesis of epoxide 2 to allylic alcohol 1 need to be identified. Concept introduction: The problem is based on the concept of enantioselective epoxidation. In this process, if a chiral epoxide needs to be formed, a racemic mixture of epoxide will be formed. Here for enantioselective epoxidation of allylic alcohols where the hydroxyl group is attached to an allylic position which is next to a C-C double bond, a catalyst is developed. This catalyst contains titanium tetraisopropoxide and enantiomer of diethyl tartrate.

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Answer 1

Question

Chapter 13, Problem 74IP

(a)

Interpretation Introduction

Interpretation:

The reagents used for the synthesis of epoxide 2 to allylic alcohol 1 need to be identified.

Concept introduction: The problem is based on the concept of enantioselective epoxidation. In this process, if a chiral epoxide needs to be formed, a racemic mixture of epoxide will be formed.

Here for enantioselective epoxidation of allylic alcohols where the hydroxyl group is attached to an allylic position which is next to a C-C double bond, a catalyst is developed. This catalyst contains titanium tetraisopropoxide and enantiomer of diethyl tartrate.

(b)

Interpretation Introduction

Interpretation:

The mechanism for the preparation of orthoester 4 from epoxide 3 needs to be proposed.

Concept Introduction: In the acid-catalyzed ring-opening of an epoxide with water, first proton transfer takes place and then nucleophilic attack takes place via an S_N2 mechanism. In the end, proton transfer step takes place that removes the charge formed after the attack of the neutral nucleophile. The general reaction is represented as follows:

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b) Certain cyclic compounds are known to be conformationally similar to carbohydrates, although they are not themselves carbohydrates. One example is Compound C shown below, which could be imagined as adopting four possible conformations. In reality, however, only one of these is particularly stable. Circle the conformation you expect to be the most stable, and provide an explanation to justify your choice. For your explanation to be both convincing and correct, it must contain not only words, but also "cartoon" orbital drawings contrasting the four structures. Compound C Possible conformations (circle one): Дет

Lab Data The distance entered is out of the expected range. Check your calculations and conversion factors. Verify your distance. Will the gas cloud be closer to the cotton ball with HCI or NH3? Did you report your data to the correct number of significant figures? - X Experimental Set-up HCI-NH3 NH3-HCI Longer Tube Time elapsed (min) 5 (exact) 5 (exact) Distance between cotton balls (cm) 24.30 24.40 Distance to cloud (cm) 9.70 14.16 Distance traveled by HCI (cm) 9.70 9.80 Distance traveled by NH3 (cm) 14.60 14.50 Diffusion rate of HCI (cm/hr) 116 118 Diffusion rate of NH3 (cm/hr) 175.2 175.2 How to measure distance and calculate rate

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Answer 2

Question

Chapter 13, Problem 74IP

(a)

Interpretation Introduction

Interpretation:

The reagents used for the synthesis of epoxide 2 to allylic alcohol 1 need to be identified.

Concept introduction: The problem is based on the concept of enantioselective epoxidation. In this process, if a chiral epoxide needs to be formed, a racemic mixture of epoxide will be formed.

Here for enantioselective epoxidation of allylic alcohols where the hydroxyl group is attached to an allylic position which is next to a C-C double bond, a catalyst is developed. This catalyst contains titanium tetraisopropoxide and enantiomer of diethyl tartrate.

(b)

Interpretation Introduction

Interpretation:

The mechanism for the preparation of orthoester 4 from epoxide 3 needs to be proposed.

Concept Introduction: In the acid-catalyzed ring-opening of an epoxide with water, first proton transfer takes place and then nucleophilic attack takes place via an S_N2 mechanism. In the end, proton transfer step takes place that removes the charge formed after the attack of the neutral nucleophile. The general reaction is represented as follows:

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Answer 3

Question

Chapter 13, Problem 74IP

(a)

Interpretation Introduction

Interpretation:

The reagents used for the synthesis of epoxide 2 to allylic alcohol 1 need to be identified.

Concept introduction: The problem is based on the concept of enantioselective epoxidation. In this process, if a chiral epoxide needs to be formed, a racemic mixture of epoxide will be formed.

Here for enantioselective epoxidation of allylic alcohols where the hydroxyl group is attached to an allylic position which is next to a C-C double bond, a catalyst is developed. This catalyst contains titanium tetraisopropoxide and enantiomer of diethyl tartrate.

(b)

Interpretation Introduction

Interpretation:

The mechanism for the preparation of orthoester 4 from epoxide 3 needs to be proposed.

Concept Introduction: In the acid-catalyzed ring-opening of an epoxide with water, first proton transfer takes place and then nucleophilic attack takes place via an S_N2 mechanism. In the end, proton transfer step takes place that removes the charge formed after the attack of the neutral nucleophile. The general reaction is represented as follows:

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Answer 4

Question

Chapter 13, Problem 74IP

(a)

Interpretation Introduction

Interpretation:

The reagents used for the synthesis of epoxide 2 to allylic alcohol 1 need to be identified.

Concept introduction: The problem is based on the concept of enantioselective epoxidation. In this process, if a chiral epoxide needs to be formed, a racemic mixture of epoxide will be formed.

Here for enantioselective epoxidation of allylic alcohols where the hydroxyl group is attached to an allylic position which is next to a C-C double bond, a catalyst is developed. This catalyst contains titanium tetraisopropoxide and enantiomer of diethyl tartrate.

(b)

Interpretation Introduction

Interpretation:

The mechanism for the preparation of orthoester 4 from epoxide 3 needs to be proposed.

Concept Introduction: In the acid-catalyzed ring-opening of an epoxide with water, first proton transfer takes place and then nucleophilic attack takes place via an S_N2 mechanism. In the end, proton transfer step takes place that removes the charge formed after the attack of the neutral nucleophile. The general reaction is represented as follows:

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Answer 5

Chapter 13, Problem 74IP

(a)

Interpretation Introduction

Interpretation:

The reagents used for the synthesis of epoxide 2 to allylic alcohol 1 need to be identified.

Concept introduction: The problem is based on the concept of enantioselective epoxidation. In this process, if a chiral epoxide needs to be formed, a racemic mixture of epoxide will be formed.

Here for enantioselective epoxidation of allylic alcohols where the hydroxyl group is attached to an allylic position which is next to a C-C double bond, a catalyst is developed. This catalyst contains titanium tetraisopropoxide and enantiomer of diethyl tartrate.

(b)

Interpretation Introduction

Interpretation:

The mechanism for the preparation of orthoester 4 from epoxide 3 needs to be proposed.

Concept Introduction: In the acid-catalyzed ring-opening of an epoxide with water, first proton transfer takes place and then nucleophilic attack takes place via an S_N2 mechanism. In the end, proton transfer step takes place that removes the charge formed after the attack of the neutral nucleophile. The general reaction is represented as follows:

Answer 6

Chapter 13, Problem 74IP

(a)

Interpretation Introduction

Interpretation:

The reagents used for the synthesis of epoxide 2 to allylic alcohol 1 need to be identified.

Concept introduction: The problem is based on the concept of enantioselective epoxidation. In this process, if a chiral epoxide needs to be formed, a racemic mixture of epoxide will be formed.

Here for enantioselective epoxidation of allylic alcohols where the hydroxyl group is attached to an allylic position which is next to a C-C double bond, a catalyst is developed. This catalyst contains titanium tetraisopropoxide and enantiomer of diethyl tartrate.

Answer 7

Chapter 13, Problem 74IP

(a)

Interpretation Introduction

Interpretation:

The reagents used for the synthesis of epoxide 2 to allylic alcohol 1 need to be identified.

Concept introduction: The problem is based on the concept of enantioselective epoxidation. In this process, if a chiral epoxide needs to be formed, a racemic mixture of epoxide will be formed.

Here for enantioselective epoxidation of allylic alcohols where the hydroxyl group is attached to an allylic position which is next to a C-C double bond, a catalyst is developed. This catalyst contains titanium tetraisopropoxide and enantiomer of diethyl tartrate.

Answer 8

(b)

Interpretation Introduction

Interpretation:

The mechanism for the preparation of orthoester 4 from epoxide 3 needs to be proposed.

Concept Introduction: In the acid-catalyzed ring-opening of an epoxide with water, first proton transfer takes place and then nucleophilic attack takes place via an S_N2 mechanism. In the end, proton transfer step takes place that removes the charge formed after the attack of the neutral nucleophile. The general reaction is represented as follows:

Answer 9

(b)

Interpretation Introduction

Interpretation:

The mechanism for the preparation of orthoester 4 from epoxide 3 needs to be proposed.

Concept Introduction: In the acid-catalyzed ring-opening of an epoxide with water, first proton transfer takes place and then nucleophilic attack takes place via an S_N2 mechanism. In the end, proton transfer step takes place that removes the charge formed after the attack of the neutral nucleophile. The general reaction is represented as follows:

Answer 10

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Answer 11

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Answer 12

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Answer 13

Ch. 13.2 - Prob. 1LTS Ch. 13.2 - Prob. 1PTS Ch. 13.2 - Prob. 2PTS Ch. 13.2 - Prob. 3ATS Ch. 13.4 - Prob. 4CC Ch. 13.5 - Prob. 2LTS Ch. 13.5 - Prob. 5PTS Ch. 13.5 - Prob. 6ATS Ch. 13.5 - Prob. 7CC Ch. 13.5 - Prob. 8CC

Solution Summary: The author explains the reagents used for synthesis of epoxide 2 to allylic alcohol 1 and the mechanism for the preparation of orthoester 4.

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